TW201605863A - Organic compound and organic optoelectric device and display device - Google Patents

Abstract

An organic compound represented by the following Chemical Formula 1, and an organic optoelectric device and a display device including the organic compound are provided. [Chemical Formula 1] In the Chemical Formula 1, X is O, S, CR<SP>a</SP> R<SP>b</SP> or SiR<SP>c</SP> R<SP>d</SP>, Y is N or CR<SP>e</SP>, at least one of Y is N, Ar1is a substituted or unsubstituted fused ring, R<SP>a</SP> to R<SP>d</SP> are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C3 to C12 heterocyclic group, or a combination thereof, R<SP>e</SP> is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group or a combination thereof.

Description

Organic compound, organic photoelectric device and display device

The present application claims the priority and the benefit of the Korean Patent Application No. 10-2014-0101213 filed on Jan. 6, 2014 in the Korean Intellectual Property Office, the entire contents of which is hereby incorporated by reference.

The invention discloses an organic compound, an organic photoelectric device and a display device.

An organic optoelectronic device is a device that converts electrical energy into light energy and is also a device that converts light energy into electrical energy.

According to its driving principle, organic optoelectronic devices can be classified as follows. One is an optoelectronic device in which excitons generated by light energy are separated into electrons and holes, and electrons and holes are transferred to different electrodes to generate electric energy; and the other is a light-emitting device in which a voltage or current is supplied to the electrodes from Electrical energy produces light energy.

Examples of the organic optoelectric device may be an organic photoelectirc device, an organic light emitting diode, an organic solar cell, and an organic photofunctional drum.

Among these, an organic light emitting diode (OLED) has recently been noted due to an increase in demand for flat panel displays. Such an organic light-emitting diode converts electrical energy into light by applying a current to the organic light-emitting material. It has a structure in which an organic layer is interposed between an anode and a cathode.

The performance of the organic light-emitting diode may be affected by the characteristics of the organic layer, and among them, it may especially be mainly affected by the organic material characteristics of the organic layer. Specifically, there is a need to develop an organic material capable of increasing hole and electron mobility while increasing electrochemical stability, so that the organic light emitting diode can be applied to a large flat panel display.

An embodiment provides an organic compound capable of realizing an organic optoelectric device having high efficiency and long life.

Another embodiment provides an organic optoelectronic device comprising the organic compound.

Yet another embodiment provides a display device including the organic optoelectronic device.

According to an embodiment, an organic compound represented by the following Chemical Formula 1 is provided. [Chemical Formula 1] In Chemical Formula 1, X is O, S, CR ^a R ^b or SiR ^c R ^d , Y is N or CR ^e , at least one Y is N, and Ar ¹ is a substituted or unsubstituted fused ring, R ^a to R ^{d is} independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C12 aryl, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof, and R ^e is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof.

In accordance with another embodiment, an organic optoelectronic device includes an anode and a cathode opposite each other and at least one organic layer interposed between the anode and the cathode, wherein the organic layer comprises the organic compound. An organic compound having excellent electrical characteristics and thermal stability is provided, and an organic light-emitting diode including the organic compound can have low driving voltage, high efficiency, high brightness, and long life characteristics.

Hereinafter, embodiments of the invention are described in detail. However, these embodiments are exemplary, and the disclosure is not limited thereto.

As used herein, the term "substituted", when not otherwise defined, refers to a C1 to C30 amine group, a nitro group, a substituted or unsubstituted group selected from the group consisting of hydrazine, halogen, hydroxy, amino, substituted or unsubstituted. Substituted C1 to C40 alkyl, C1 to C30 alkyl, C1 to C10 alkylalkyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C6 to C30 heterocyclic Substituting a substituent of a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group (e.g., a trifluoromethyl group, etc.), a cyano group, a carboxyl group, or a combination thereof, in place of the substituent or at least one hydrogen of the compound.

Further, from substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C3 to C40 alkyl, C1 to C30 alkyl, C1 to C10 Alkylalkyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C3 to C30 heterocyclyl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl (eg, three Two adjacent substituents selected from a fluoromethyl group, a cyano group, a carboxyl group or a combination thereof may be fused to each other to form a ring. For example, a substituted C6 to C30 aryl group can be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted anthracene ring.

In the present specification, when a specific definition is not additionally provided, "hetero" means that one to three hetero atoms selected from N, O, S, P, and Si are contained in one functional group, and the balance is carbon.

As used herein, the term "aryl" refers to all of the elements of the ring having a substituent that forms a conjugated p-orbital, and may be a monocyclic, polycyclic or fused-ring polycyclic (ie, ring-shared adjacent pairs of carbon atoms) functional groups. .

As used herein, the term "heterocyclyl" may refer to an aryl or cycloalkyl group containing from 1 to 3 heteroatoms selected from N, O, S, P, and Si in one functional group and the remainder being carbon. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may contain a hetero atom.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and/or substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted phenyl, substituted or unsubstituted. Substituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl, substituted Or unsubstituted biphenyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted biphenyl, substituted or not Substituted isoquarter phenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl group, substituted or unsubstituted Substituted indenyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenylthio, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or Unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted Azolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or Unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzene And a thienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group , substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, Substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenylpyrazine, substituted or unsubstituted phenothiazine, substituted or not Substituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuran The butyl group, the substituted or unsubstituted dibenzothiophenyl group, the substituted or unsubstituted carbazolyl group, a combination thereof or a combination of the foregoing groups is fused, but not limited thereto.

In the present specification, the hole characteristic refers to a feature capable of supplying electrons to form a hole when an electric field is applied due to a conductive characteristic according to a HOMO level, and a hole formed in the anode is easily injected into the light-emitting layer and in the light-emitting layer. The characteristics of the transmission.

In addition, the electronic feature refers to a feature capable of receiving electrons when an electric field is applied due to a conductive characteristic according to the LUMO level, and a feature that electrons formed in the cathode are easily injected into the light-emitting layer and transmitted in the light-emitting layer.

Hereinafter, an organic compound according to an embodiment will be described.

The organic compound according to an embodiment is represented by the following Chemical Formula 1. [Chemical Formula 1] In Chemical Formula 1, X is O, S, CR ^a R ^b or SiR ^c R ^d , Y is N or CR ^e , at least one Y is N, and Ar ¹ is a substituted or unsubstituted fused ring, R ^a to R ^{d is} independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C12 aryl, a substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof, and R ^e is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof.

The organic compound represented by Chemical Formula 1 has a structure in which a ring containing at least one nitrogen is bonded to a substituted or unsubstituted fused ring.

The ring containing at least one nitrogen has polarity and thus can interact with the electrode, thus facilitating the injection of charge. Further, the ring containing at least one nitrogen may have a structure that easily receives electrons when an electric field is applied thereto, and thus the driving voltage of the organic photoelectric device including the organic compound can be reduced.

Furthermore, a structure comprising a ring of at least one nitrogen bonded to a substituted or unsubstituted fused ring may advantageously balance between the holes and the electrons, thus increasing the efficiency of the organic optoelectronic device comprising the organic compound.

Further, the organic compound may have a bipolar structure formed by appropriately arranging a substituent, and thus the flow of holes and electrons is appropriately balanced, with the result that the efficiency of the organic photoelectric device including the organic compound is improved.

In Chemical Formula 1, at least one of Y may be nitrogen (N), and may include, for example, two or three nitrogens (N).

In Chemical Formula 1, Ar ¹ may be a fused ring that binds two rings or more than two rings, for example, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, substituted or Unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl or substituted or unsubstituted tert-triphenyl, but the invention is not limited thereto.

For example, Ar ^{1 of} Chemical Formula 1 may be selected from the groups listed in Group 1 below. [Group 1] In Group 1, R ¹ to R ^{9 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted a substituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C4 to C30 arylamino group, wherein the substituted group is, for example, a halogen or a cyano group. a group substituted with a hydroxyl group, an amine group, a nitro group, a carboxyl group or a combination thereof, and * represents a point of attachment to the chemical formula 1.

For example, at least R ^e in Chemical Formula 1 may comprise a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof. The aryl and/or heteroaryl group can be, for example, a non-fused ring (e.g., phenyl, biphenyl, terphenyl or biphenyl) or a fused ring (e.g., naphthyl, anthracenyl or phenanthryl).

The organic compound can be represented, for example, by the following Chemical Formula 2 or Chemical Formula 3 depending on the position and amount of nitrogen. [Chemical Formula 2] [Chemical Formula 3] In Chemical Formula 2 or Chemical Formula 3, X, A ^r1 and R ^a to R ^d is as defined above, and R ^e1 and R ^e2 and R ^e same.

In Chemical Formula 2 or Chemical Formula 3, for example, at least one of R ^e1 and R ^e2 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group or combination. The aryl and/or heteroaryl group can be, for example, a non-fused ring (e.g., phenyl, biphenyl, terphenyl or biphenyl) or a fused ring (e.g., naphthyl, anthracenyl or phenanthryl).

For example, at least one of R ^e1 and R ^e2 may be represented by the following chemical formula A. [Chemical Formula A] *-L-Ar ² In Chemical Formula A, * represents a point of attachment to Chemical Formula 2 or Chemical Formula 3, L is a single bond, substituted or unsubstituted C1 to C30 alkyl group, substituted or not Substituted C3 to C30 cycloalkylene, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 An aryl group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, a combination thereof or a combination fused ring of the foregoing groups.

Ar ² may comprise one of the groups listed in Group 2 below. [Group 2] In Group 2, R ¹⁰ to R ^{75 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted a substituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C4 to C30 arylamino group, wherein the substituted group is, for example, a halogen or a cyano group. a group substituted with a hydroxyl group, an amine group, a nitro group, a carboxyl group or a combination thereof, and * represents a point of attachment to L.

The organic compound can be represented, for example, by one of the following Chemical Formulas 4 to 35. [Chemical Formula 4] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 9] [Chemical Formula 11] [Chemical Formula 11] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 19] [Chemical Formula 19] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25] [Chemical Formula 25] [Chemical Formula 27] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 34] [Chemical Formula 34] [Chemical Formula 35] In Chemical Formula 4 to Chemical Formula 35, R ¹ to R ^9, R ^a to R ^d, R ^e1 and R ^e2 are as defined above.

The organic compound may, for example, be one of the compounds listed in the following Group 3, but is not limited thereto. [Group 3] .

The organic compound can be used in an organic optoelectric device.

Hereinafter, an organic photoelectric device to which the organic compound is applied will be described.

The organic optoelectric device may be any device for converting electric energy into light energy and converting the light energy into electric energy, and is not particularly limited, and may be, for example, an organic optoelectric device, an organic light emitting diode, an organic solar cell, and an organic light guide. drum.

The organic optoelectric device includes an anode and a cathode opposite to each other and at least one organic layer interposed between the anode and the cathode, wherein the organic layer contains the organic compound.

Herein, an organic light-emitting diode as an example of an organic photoelectric device is described with reference to the drawings.

1 and 2 are cross-sectional views of respective organic light emitting diodes according to an embodiment.

Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 opposed to each other and an organic layer 105 interposed between the anode 120 and the cathode 110.

The anode 120 can be made of a conductor having a high work function to aid in hole injection, and can be, for example, a metal, a metal oxide, and/or a conductive polymer. The anode 120 may be, for example, metallic nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (indium tin oxide) Indium zinc oxide; IZO); etc.; combinations of metals and oxides, such as ZnO and Al or SnO ₂ and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(extended ethyl) 1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

Cathode 110 can be made of a conductor having a low work function to aid in electron injection, and can be, for example, a metal, a metal oxide, and/or a conductive polymer. The cathode 110 may be, for example, a metal or an alloy thereof such as magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, lead, antimony, bismuth, etc.; a multilayer structural substance such as LiF/Al _{, LiO 2 / Al, LiF /} Ca, LiF / Al , and BaF ₂ / Ca, but is not limited thereto.

The organic layer 105 includes a light emitting layer 130.

The light emitting layer 130 may comprise, for example, a separate organic compound, a mixture of at least two organic compounds.

The organic compound may be included as a main body of the light-emitting layer 130, such as a phosphorescent host.

The light emitting layer 130 may further include a dopant. The dopant can be a red, green or blue dopant such as a phosphorescent dopant.

A small amount of dopant is mixed with the host to cause luminescence, and the dopant may generally be a substance that emits light by multiple excitations to a triplet state or a triplet state, such as a metal complex. The dopant may be, for example, an inorganic, organic or organic/inorganic compound, and one or more kinds thereof may be used.

The phosphorescent dopant may be an organometallic compound comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto. [Chemical Formula Z] L ₂ MX In the chemical formula Z, M is a metal, and L and X are the same or different, and are ligands which form a complex with M.

M may, for example, be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and L and X may, for example, be bidentate ligands (bidendate) Ligand).

Referring to FIG. 2 , the organic light emitting diode 200 further includes a hole assisting layer 140 and a light emitting layer 130 . The hole assist layer 140 may increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 230 and block electrons. The hole assisting layer 140 may be, for example, a hole transport layer (HTL), a hole injection layer (HIL), and/or an electron blocking layer (EBL), and may include at least one Floor.

Furthermore, in an embodiment of the present invention, in FIG. 1 or FIG. 2, the organic light emitting diode may further include an electron transport layer (ETL) and an electron injection layer in the organic layer 105. Layer; EIL), hole injection layer (HIL), and the like.

In addition to the light emitting layer 130, the organic compound may be included in at least one of an electron transport layer (ETL) and an electron injection layer (EIL).

The organic light-emitting diode 100 and the organic light-emitting diode 200 can be manufactured by forming an anode or a cathode on a substrate, and forming an organic layer according to a dry coating method such as evaporation, sputtering, plasma plating, and ion plating. And forming a cathode or an anode thereon.

The organic light emitting diode can be applied to an organic light emitting diode (OLED) display.

In the following, embodiments are explained in more detail with reference to examples. However, these examples are not to be construed as limiting the scope of the invention in any way. Synthesis Example of Organic Compound Example 1 : Synthesis Intermediate M-6

The intermediate M-6 was synthesized as a specific example of the compound according to the present invention by the following six steps in Reaction Scheme 1. [Reaction Scheme 1] First step: synthesis of intermediate products ( M-1 )

Add 50.0 g (437.9 mmol) of 2-naphthol (naphthalene-2-ol) and 77.9 g (437.9 mmol) of N-bromosuccinimide (NBS) to 600 in a 1000 mL flask. In 5% acetonitrile, the mixture was stirred at room temperature for 12 hours under a stream of nitrogen. The obtained mixture was added to 3000 ml of distilled water, and the solid crystals therein were dissolved in 1,2-dichloromethane, filtered with aerogel/diatomaceous earth, and then the appropriate amount was removed therefrom. The organic solvent was recrystallized from methanol to give Intermediate M-1 (87.1 g, yield 89%). Calculated (calcd.) C10H7BrO: C, 53.84; H, 3.16; Br, 35.82; O, 7.17; Found: C, 53.82; H, 3.11; Br, 35.63; O, 7.11 Second Step : Synthesis Intermediate product (M-2)

77.0 g (345.2 mmol) of intermediate M-1 and 95.4 g (690.4 mmol) of potassium carbonate were added to 1000 mL of N,N-dimethylformamide in a 2000 mL Erlenmeyer flask at 0 °C. 32.2 ml (517.7 mmol) of methyl iodide (MeI) was slowly added in a dropwise fashion. Then, the mixture was stirred at room temperature for 12 hours under a nitrogen stream. The obtained mixture was added to 3000 ml of distilled water, and the solid crystals therein were filtered to give Intermediate M-2 (101.1 g, yield 83%). For C11H9BrO: C, 55.72; H, 3.83; Br, 33.70; O, 6.75; Found: C, 55.36; H, 3.71; Br, 33.29; O, 6.46 Third Step : Synthesis of Intermediate (M-3)

80.0 g (337.4 mmol) of intermediate M-2, 102.8 g (404.9 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'- Bis-1,3,2-dioxaborane (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane , 16.57 g (20.3 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) Pd(dppf)Cl ₂ ) and 99.4 g (1012.3 mmol) of potassium acetate (KOAc) were added to 1000 mL of toluene in a 2000 mL flask, and the mixture was heated at 110 ° C for 12 hours under a nitrogen stream. The obtained mixture was added to 2000 mL of methanol, and the solid crystals were filtered, and the intermediate M-3 (38.0 g, yield 40%) was obtained by column chromatography. Calculated C17H21BO3: C, 71.86; H, 7.45; B, 3.80; O, 16.89; Found: C, 71.36; H, 7.18; B, 3.53; O, 16.27 Step 4: Synthesis of intermediate product ( M-4 )

38.0 g (174.4 mmol) of intermediate M-3, 52.0 g (183.1 mmol) of 2,4,5,6-tetrachloropyrimidine, 60.2 g (436.0 mmol) of potassium carbonate and 10.1 g (8.7 mmol) Tetrakis (triphenylphosphine) palladium (Pd(PPh ₃ ) ₄ ) was added to 600 mL of 1,4-dioxane and 300 mL of water in a 2000 mL flask. The mixture was heated at 65 ° C for 12 hours under a stream of nitrogen. The obtained mixture was added to 1000 mL of methanol, and the solid crystals therein were filtered, dissolved in chlorobenzene, filtered with a hydrazine gel/celella, and then methanol was removed after removing an appropriate amount of organic solvent. Recrystallization gave intermediate M-4 (46.6 g, yield 75%). Calcd for C15H9Cl3N2O: C, 53.05; H, 2.67; Cl, 31.32; N, 8.25; O, 4.71; Found: C, 52.95; H, 2.34 ; Cl, 31.15; N, 8.20; O, 4.64 Fifth Step: Synthetic intermediate ( M-5 )

46.0 g (135.5 mmol) of intermediate M-4 was dissolved in 500 mL of dichloromethane (MC) in a 2000 mL flask and 270 mL (270.0 mmol) of boron tribromide was dropped (27 mL). Boranetribromide, BBr ₃ ) was slowly added while maintaining the solution at 0 °C. When the reaction was completed, the mixture was washed with an aqueous sodium thiosulfate solution, and organic solvent was removed therefrom to give Intermediate M-5 (32.3 g, yield 80%). Calcd for C14H7Cl3N2O: C, 51.65; H, 2.17; Cl, 32.67; N, 8.60; O, 4.91; Found: C, 51.46; H, 2.05 ; Cl, 32.53; N, 8.41; O, 4.38 Sixth Step: Synthetic intermediate ( M-6 )

Add 32.0 g (98.3 mmol) of intermediate M-5 and 24.4 g (127.8 mmol) of copper (I) thiophene-2-carboxylate (CuTC) to 500 mL in a 1000 mL flask. The mixture was refluxed at 190 ° C for 48 hours in N,N-dimethylacetamide (DMAc). After removing the organic solvent from the mixture, the intermediate M-6 (24.7 g, yield 87%) was obtained by column chromatography. For C14H6Cl2N2O: C, 58.16; H, 2.09; Cl, 24.53; N, 9.69; O, 5.53; found: C, 58.06; H, 2.01; Cl, 24.49; N, 9.53; O, 5.42 Example 2 : Synthesis Intermediates N-6 , O-6 , P-6 , Q-6 , R-6

The intermediates N-6, O-6, P-6, Q-6, R-6 were synthesized as the specific examples of the compound according to the present invention by the six steps of the same [Reaction Scheme 2] as in Example 1. In this context, 2-thionaphthol (naphthalene-2-thiol), naphthalen-1-ol, naphthalene-1-thiol, 9-phenanthrene (phenanthren) are used, respectively. -9-ol), 9- thiophenanthrene (phenanthren-9-thiol) is substituted according to the [Reaction Scheme 1] method in the synthesis step 1 of [Reaction Scheme 1] as a starting material of 2-naphthol to prepare N -5, O-5, P-5, Q-5 and R-5. [Reaction Scheme 2] Example 3 : Synthesis of intermediates S-6 , T-6 , U-6

The intermediate S-6 was synthesized as a specific example of the compound according to the present invention by the following three steps of [Reaction Scheme 3]. Further, in the middle of a specific example of the compound according to the present invention, by the same method as the method of synthesizing the intermediate S-6 in the following [Reaction Scheme 3], using the starting materials of the following T-3 and U-3 T-6 and U-6. [Reaction Scheme 3] First step: synthesis of intermediate S-4

56.0 g (171.7 mmol) of intermediate S-3, 30.0 g (163.6 mmol) of 2,4,6-trichloropyrimidine, 56.5 g (408.9 mmol) of potassium carbonate and 9.5 g (8.2 mmol) of four ( Triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) was added to 540 mL of 1,4-dioxane and 270 mL of water in a 2000 mL Erlenmeyer flask, and the mixture was heated under a nitrogen stream and refluxed for 6 hours. The obtained mixture was added to 1100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give intermediate S-4 (42.3 g, yield 71%). Calculated for C17H12Cl2N2O2: C, 58.81; H, 3.48; Cl, 20.42; N, 8.07; O, 9.22; Found: C, 58.63; H, 3.23 ; Cl, 20.38; N, 8.01; O, 9.15; a second step :Synthesis Intermediate S-5

40.0 g (115.2 mmol) of intermediate S-4 and 500 mL of anhydrous tetrahydrofuran (THF) were placed in a 2000 mL flask and 1.5 M of methyllithium in 210 mL of diethyl ether was added dropwise at -70 °C. LiCH ₃ ) was added thereto, and the mixture was stirred at the temperature for 2 hours. When the reaction was completed, 100 mL of ice water was added thereto and 300 mL of 50% acetic acid was added. Thereafter, the organic layer was separated therefrom, washed twice with distilled water, dried, and evaporated under vacuum. Then, the residual colorless solid was recrystallized from heptane / toluene to give Intermediate S-5 (32.7 g, yield 81%). Calcd 17H14Cl2N2O: C, 61.28; H, 4.23; Cl, 21.28; N, 8.41; O, 4.80; Found: C, 61.11; H, 4.03 ; Cl, 21.24; N, 8.40; O, 4.78 Third Step: Synthetic intermediate S-6

30.0 g (90.0 mmol) of intermediate S-5 was dissolved in 450 mL of anhydrous 1,2-dichloromethane (MC) in a 1000 mL flask and slowly dropped 15.0 g (94.5 mmol) of three Boron trifluoride-diethyletherate (BF ₃ •Et ₂ O) was added for 10 minutes. The mixture was heated to 50 ° C and stirred for 2 hours. The resultant was cooled to room temperature, distilled water was added thereto, and the mixture was extracted three times with diethyl ether. Next, the organic layer obtained therefrom was dried over anhydrous magnesium sulfate. After the solvent was removed therefrom, the concentrated residue was separated and purified by silica gel chromatography to afford Intermediate S-6 (16.7 g, yield 55%). For C17H12Cl2N2: C, 64.78; H, 3.84; Cl, 22.50; N, 8.89; Found: C, 64.71; H, 3.78; Cl, 22.35; N, 8.62 Example 4 : Synthesis Intermediate V-6 , W- 6 , X-6

The intermediate V-6 was synthesized as a specific example of the compound according to the present invention by the following two steps of [Reaction Scheme 4]. Further, an intermediate which is a specific example of the compound according to the present invention is synthesized by the same method as the method of synthesizing the intermediate V-6 in the following [Reaction Scheme 4] using W-4 and X-4 as starting materials. -6 and X-6. [Reaction Scheme 4] First step: synthesis of intermediate V-5

53.6 g (171.7 mmol) of intermediate V-4, 30.0 g (163.6 mmol) of 2,4,6-trichloropyrimidine, 56.5 g (408.9 mmol) of potassium carbonate and 9.5 g (8.2 mmol) of four ( Triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) was added to 540 mL of 1,4-dioxane and 270 mL of water in a 2000 mL flask and the mixture was heated under reflux for 8 hours. The obtained mixture was added to 1100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/diatomaceous earth, and then an appropriate amount of organic solvent was removed therefrom. After recrystallization from methanol, intermediate V-5 (43.5 g, yield 76%) was obtained. Calcd C16H14Cl2N2Si: C, 57.66; H, 4.23; Cl, 21.27; N, 8.41; Si, 8.43; Found: C, 57.60; H, 4.21 ; Cl, 21.19; N, 8.35; Si, 8.39; a second step : Synthesis Intermediate V-6

40.0 g (120.2 mmol) of intermediate V-5 and 2.2 g (2.4 mmol) of tris(triphenylphosphine) rhodium (I), RhCl(PPh ₃ ) ₃ ) In a 1000 flask, 600 mL of 1,4-dioxane was added thereto by dropping, and the mixture was heated under a nitrogen stream and refluxed for 8 hours. When the reaction was completed, after the organic layer was removed therefrom, the resultant was treated by column chromatography to give Intermediate V-6 (21.87 g, yield: 55 %). For C16H12Cl2N2Si: C, 58.01; H, 3.65; Cl, 21.40; N, 8.46; Si, 8.48; found: C, 57.89; H, 3.58; Cl, 21.36; N, 8.41; Si, 8.41 Example 5 : Synthesis Compound A-13

Compound A-13 was synthesized as a specific example of the compound according to the present invention by the following two steps. First step: synthesis of intermediate M-6-13

4.0 g (13.8 mmol) of intermediate M-6, 5.4 g (14.5 mmol) of phenyl-3-boronic ester-carbazole, 4.8 g (34.6 mmol) Potassium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine)palladium were added to 50 mL of 1,4-dioxane and 25 Ml of water in a 250 mL flask, and the mixture was heated under a nitrogen stream and refluxed for 6 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were dissolved in monochlorobenzene, filtered with a decyl gel/diatomaceous earth, and then after removing an appropriate amount of the organic solvent therefrom. Methanol was recrystallized to give intermediate M-6-13 (5.62 g, yield 78%). Calcd for C32H18ClN3O: C, 77.49; H, 3.66; Cl, 7.15; N, 8.47; O, 3.23; Found: C, 77.25; H, 3.46 ; Cl, 7.12; N, 8.45; O, 3.34; a second step : Synthesis Intermediate A-13

5.5 g (11.2 mmol) of intermediate M-6-13, 1.9 g (11.7 mmol) of carbazole, 2.1 g (22.4 mmol) of sodium t-butoxide, 1.1 g (0.6 Ment) of tris(dibenzylideneacetone) dipalladium (0) and 0.9 mL of trit-butylphosphine (50% in toluene) In 75 mL of xylene in a 250 mL round flask, the mixture was heated under a stream of nitrogen and refluxed for 15 hours. The obtained mixture was added to 200 mL of methanol, and the solid crystals therein were filtered, dissolved in dichlorobenzene, filtered with a hydrazine gel/celella, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-13 (5.3 g, yield 76%). Calculated for C44H26N4O: C, 84.33; H, 4.18; N, 8.94; O, 2.55; Found: C, 84.32; H, 4.11; N, 8.85; O, 2.49 Example 6 : Synthesis of Compound A-17

Compound A-17 was synthesized as a specific example of the compound according to the present invention by the following first step. First step: synthesis of compound A-17

2.3 g (8.0 mmol) of intermediate M-6, 2.8 g (16.8 mmol) of carbazole, 1.5 g (16.0 mmol) of sodium tributoxide, 0.5 g (0.8 mmol) of tris(dibenzylidene) The base acetone) dipalladium (0) and 0.6 mL of tri-tert-butylphosphine (50% in toluene) were added to 50 mL of xylene in a 100 mL round flask, and heated under a nitrogen stream and the mixture was refluxed for 15 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in dichlorobenzene, filtered with a decyl gel/celella, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-17 (3.5 g, yield 70%). For C38H22N4O: C, 82.89; H, 4.03; N, 10.18; O, 2.91; Found: C, 82.79; H, 4.01; N, 10.11; O, 2.89 Example 7 : Synthesis of Compound A-33

Compound A-33 was synthesized as a specific example of the compound according to the present invention by the following two steps. First step: synthesis of intermediate M-6-33

20.0 g (69.18 mmol) of intermediate M-6, 8.9 g (72.63 mmol) of phenylboronic acid, 23.9 g (172.9 mmol) of potassium carbonate and 4.0 g (3.5 mmol) of tetrakis(triphenylphosphine)palladium were added. 200 mL of 1,4-dioxane and 100 mL of water in a 500 mL flask were heated under a stream of nitrogen and the mixture was refluxed for 8 hours. The obtained mixture was added to 400 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/celella, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give intermediate M-6-33 (18.7 g, yield 78%). Calcd for C20H11ClN2O: C, 72.62; H, 3.35; Cl, 10.72; N, 8.47; O, 4.84; Found: C, 72.60; H, 3.32 ; Cl, 10.52; N, 8.37; O, 4.80; a second step :Synthesis Compound A-33

4.0 g (12.1 mmol) of intermediate M-6-33, 5.5 g (12.7 mmol) of M-6-33-1, 4.2 g (30.2 mmol) of potassium carbonate and 0.7 g (0.6 mmol) of four ( Triphenylphosphine)palladium was added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask and heated under a stream of nitrogen and the mixture was refluxed for 8 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-33 (5.4 g, yield 71%). Calculated for C44H28N2O: C, 87.97; H, 4.70; N, 4.66; O, 2.66; Found: C, 87.64; H, 4.62 ; N, 4.60; O, 2.47; 8 Example: Synthesis of Compound A-37

Compound A-37 was synthesized as a specific example of the compound according to the present invention by the following procedure. First step: synthesis of compound A-37

4.0 g (12.1 mmol) of intermediate M-6-33, 6.5 g (12.7 mmol) of M-6-37, 4.2 g (30.2 mmol) of potassium carbonate and 0.7 g (0.6 mmol) of tetrakis (triphenyl) Palladium was added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask and heated under a stream of nitrogen and the mixture was refluxed for 10 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-37 (6.36 g, yield 74%). Calculated for C50H32N2O: C, 88.73; H, 4.77; N, 4.14; O, 2.36; Found: C, 88.15; H, 4.29; N, 4.11; O, 2.26; Example 9 : Synthesis of Compound A-41

Compound A-41 was synthesized as a specific example of the compound according to the present invention by the following procedure. First step: synthesis of compound A-41

4.0 g (12.1 mmol) of intermediate M-6-33, 6.4 g (12.7 mmol) of M-6-41, 4.2 g (30.2 mmol) of potassium carbonate and 0.7 g (0.6 mmol) of tetrakis (triphenyl) Palladium was added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask and heated under a stream of nitrogen and the mixture was refluxed for 10 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-41 (5.48 g, yield: 64%). Calculated C50H30N2O: C, 89.00; H, 4.48; N, 4.15; O, 2.37; Found: C, 88.59; H, 4.33; N, 4.07; O, 2.21; Example 10 : Synthesis of Compound A-113

Compound A-113 was synthesized as a specific example of the compound according to the present invention by the following procedure. First step: synthesis of compound A-113

4.0 g (12.1 mmol) of intermediate M-6-33, 4.7 g (12.7 mmol) of M-6-113, 4.2 g (30.2 mmol) of potassium carbonate and 0.7 g (0.6 mmol) of tetrakis (triphenyl) Palladium was added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask and heated under a stream of nitrogen and the mixture was refluxed for 8 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-113 (4.65 g, yield 68%). Calculated C38H22N2O2: C, 84.74; H, 4.12; N, 5.20; O, 5.94; Found: C, 84.37; H, 4.03; N, 5.10; O, 5.84; Example 11 : Synthesis of Compound A-117

Compound A-117 was synthesized as a specific example of the compound according to the present invention by the following procedure. First step: synthesis of compound A-117

4.0 g (12.1 mmol) of intermediate M-6-33, 5.6 g (12.7 mmol) of M-6-117, 4.2 g (30.2 mmol) of potassium carbonate and 0.7 g (0.6 mmol) of tetrakis (triphenyl) Palladium was added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask and heated under a stream of nitrogen and the mixture was refluxed for 10 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-117 (5.5 g, yield 71%). Calculated for C45H28N2O: C, 88.21.; H, 4.61; N, 4.57; O, 2.61; Found: C, 88.17; H, 4.54; N, 4.43; O, 2.43; Example 12 : Synthesis of Compound A-109

Compound A-109 was synthesized as a specific example of the compound according to the present invention by the following procedure. First step: synthesis of compound A-109

4.0 g (7.1 mmol) of intermediate M-6-33, 3.1 g (7.5 mmol) of phenyl-3,3-bicarbazole, 1.4 g (14.2 mmol) of sodium third butoxide, 0.4 g (0.7 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.6 mL of tri-tert-butylphosphine (50% in toluene) were added to 50 mL of xylene in a 100 mL round flask and The mixture was heated under a stream of nitrogen and refluxed for 15 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in dichlorobenzene, filtered with a decyl gel/celella, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-109 (3.6 g, yield 72%). Calculated C50H30N4O: C, 85.45; H, 4.30; N, 7.97; O, 2.28; Found: C, 85.33; H, 4.24; N, 7.89; O, 2.15 Example 13 : Synthesis of Compound B-109

Compound B-109 was synthesized as a specific example of the compound according to the present invention by the following two steps. First step: synthesis of intermediate N-6-109

10.0 g (32.8 mmol) of intermediate N-6, 4.2 g (34.4 mmol) of phenylboronic acid, 11.3 g (81.9 mmol) of potassium carbonate and 1.9 g (1.6 mmol) of tetrakis(triphenylphosphine)palladium 100 mL of 1,4-dioxane and 50 mL of water in a 250 mL flask were added and heated under a stream of nitrogen and the mixture was refluxed for 10 hours. The obtained mixture was added to 200 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a methoxygel/algae earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give the compound N-6-109 (7.6 g, yield: 64%). Calculated for C20H11ClN2S: C, 69.26; H, 3.20; Cl, 10.22; N, 8.08; S, 9.25; Found: C, 69.19; H, 3.07 ; Cl, 10.17; N, 8.01; S, 9.09; a second step :Synthesis Compound B-109

4.0 g (6.9 mmol) of intermediate N-6-109, 3.0 g (7.3 mmol) of phenyl-3,3-bicarbazole, 1.3 g (13.9 mmol) of sodium third butoxide, 0.4 g (0.7 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.6 mL of tri-tert-butylphosphine (50% in toluene) were added to 50 mL of xylene in a 100 mL round flask and The mixture was heated under a stream of nitrogen and refluxed for 15 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound B-109 (3.2 g, yield: 64%). Calculated for C50H30N4S: C, 83.54; H, 4.21.; N, 7.79; S, 4.46; Found: C, 83.39; H, 4.11; N, 7.68; S, 4.39; Example 14 : Synthesis of Compound A-111

Compound A-111 was synthesized as a specific example of the compound according to the present invention by the following two steps. First step: synthesis of intermediate O-6-111

10.0 g (34.6 mmol) of intermediate O-6, 4.4 g (36.3 mmol) of phenylboronic acid, 12.0 g (86.5 mmol) of potassium carbonate and 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium 100 mL of 1,4-dioxane and 50 mL of water in a 250 mL flask were added and heated under a stream of nitrogen and the mixture was refluxed for 6 hours. The obtained mixture was added to 200 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a methoxygel/algae earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give the intermediate O-6-111 (8.9 g, yield 74%). Calcd for C20H11ClN2O: C, 72.62; H, 3.35; Cl, 10.72; N, 8.47; O, 4.84; Found: C, 72.36; H, 3.11 ; Cl, 10.53; N, 8.29; O, 4.65; a second step : Synthesis Compound A-111

4.0 g (7.1 mmol) of intermediate O-6-111, 3.1 g (7.5 mmol) of phenyl-3,3-bicarbazole, 1.4 g (14.2 mmol) of sodium third butoxide, 0.4 g (0.7 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.6 mL of tri-tert-butylphosphine (50% in toluene) were added to 50 mL of xylene in a 100 mL round flask and The mixture was heated under a stream of nitrogen and refluxed for 15 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in dichlorobenzene, filtered with a decyl gel/celella, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound A-111 (3.3 g, yield 66%). Calculated C50H30N4O: C, 85.45; H, 4.30; N, 7.97; O, 2.28; Found: C, 85.17; H, 4.20; N, 7.77; O, 2.19 Example 15 : Synthesis of Compound B-111

Compound B-111 was synthesized as a specific example of the compound according to the present invention by the following two steps.

10.0 g (32.8 mmol) of intermediate P-6, 4.2 g (34.4 mmol) of phenylboronic acid, 11.3 g (81.9 mmol) of potassium carbonate and 1.9 g (1.6 mmol) of tetrakis(triphenylphosphine)palladium 100 mL of 1,4-dioxane and 50 mL of water in a 250 mL flask were added and heated under a stream of nitrogen and the mixture was refluxed for 10 hours. The obtained mixture was added to 200 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a methoxygel/algae earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound P-6-111 (8.0 g, yield 67%). Calculated for C20H11ClN2S: C, 69.26; H, 3.20; Cl, 10.22; N, 8.08; S, 9.25; Found: C, 69.08; H, 3.04 ; Cl, 10.12; N, 7.89; S, 9.16; a second step : synthesis of compound B-111

4.0 g (6.9 mmol) of intermediate P-6-111, 3.0 g (7.3 mmol) of phenyl-3,3-bicarbazole, 1.3 g (13.9 mmol) of sodium third butoxide, 0.4 g (0.7 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.6 mL of tri-tert-butylphosphine (50% in toluene) were added to 50 mL of xylene in a 100 mL round flask and The mixture was heated under a stream of nitrogen and refluxed for 15 hours. The obtained mixture was added to 100 mL of methanol, and the solid crystals therein were filtered, dissolved in monochlorobenzene, filtered with a decyl gel/alkali earth, and then after removing an appropriate amount of organic solvent, Methanol was recrystallized to give Compound B-111 (3.5 g, yield 70%). Calculated C50H30N4S: C, 83.54; H, 4.21; N, 7.79; S, 4.46; Found: C, 83.32; H, 4.05; N, 7.71; S, 4.44; Comparative Example 1 : Synthesis of CBP

The compound represented by the following chemical formula a is synthesized in the same manner as disclosed in International Publication No. WO 2013032035. Chemical formula a Assessment 1 : Comparison of simulated characteristics of organic compounds

The energy levels of each compound were measured using a supercomputer GAIA (IBM power 6) by the Gaussian 09 method, and the results are provided in Table 1 below. (Table 1)

Please refer to Table 1, because the excellent electron transport characteristics expected in the simulation fall within the HOMO level of about -4.9 eV to -5.9 eV and the range of about -1.6 eV to -2.1 eV LUMO, the organic compound of Comparative Example 1 meets The HOMO level did not meet the LUMO level, so the organic compound compared to Examples 5 to 15 showed an imbalance between the hole and the electron. The organic compounds of Examples 5 to 15 have an appropriate energy level, and thus it is expected to have excellent efficiency and longevity compared to the organic compound of Comparative Example 1. Manufacturing Organic Light Emitting Dimer Example 16

An organic light-emitting diode was fabricated by using the compound A-13 of Example 5 as a host and (piq) ₂ Ir(acac) as a dopant.

For the anode, ITO having a thickness of 1000 Å was used, and regarding the cathode, aluminum (Al) having a thickness of 1000 Å was used. Specifically, a method of manufacturing an organic light-emitting diode is described by cutting an ITO glass substrate having a sheet resistance of 15 Ω/cm ² into a size of 50 mm × 50 mm × 0.7 mm, respectively, in acetone, isopropyl The alcohol and pure water were ultrasonically washed for 15 minutes and washed with ultraviolet ozone for 30 minutes.

On the substrate, N4,N4'-bis(naphthalen-1-yl)-N4,N'4- was deposited by a deposition rate of 0.1 nm/s to 0.3 nm/s under a vacuum of 650×10 ^-7 Pa. Diphenylbiphenyl-4,4'-diamine (N4, N4'-di(naphthalen-1-yl)-N4, N4'-diphenylbiphenyl-4,4'-diamine, NPB) to form a thickness of 800 Å Hole Transport Layer (HTL). Then, the compound A-13 of Example 5 was used under the same vacuum deposition conditions to form a light-emitting layer having a thickness of 300 Å, and at this time, a phosphorescent dopant (piq) ₂ Ir(acac) was deposited. Here, the phosphorescent dopant was deposited to be 3 wt% based on the total weight of the light-emitting layer of 100 wt% by adjusting the deposition rate.

On the luminescent layer, a hole barrier layer having a thickness of 50 Å was formed by depositing bis(2-methyl-8-quinolinyl)-4-(phenylphenol)aluminum (BAlq) under the same vacuum deposition conditions. Subsequently, an electron transport layer (ETL) having a thickness of 200 Å was formed by depositing Alq3 under the same vacuum deposition conditions. On the electron transport layer (ETL), an organic photovoltaic device is fabricated by sequentially depositing LiF and Al to form a cathode.

The organic optoelectric device has the following structure: ITO/NPB (80 nm) / EML (A-13 (97 wt%) + (piq) ₂ Ir(acac) (3 wt%), 30 nm) / Balq (5 nm) / Alq3 20 nm / LiF (1 nm) / Al (100 nm). Example 17

An organic light-emitting diode was fabricated according to the same procedure as in Example 16 except that Compound A-17 of Example 6 was used instead of Compound A-13 of Example 5. Example 18

An organic light-emitting diode was fabricated according to the same procedure as in Example 16 except that Compound A-33 of Example 7 was used instead of Compound A-13 of Example 5. Example 19

An organic light-emitting diode was fabricated according to the same method as Example 16 except that the compound A-37 of Example 8 was used instead of the compound A-13 of Example 5. Example 20

An organic light-emitting diode was fabricated according to the same procedure as in Example 16 except that Compound A-41 of Example 9 was used instead of Compound A-13 of Example 5. Example 21

An organic light-emitting diode was fabricated according to the same procedure as in Example 16 except that Compound A-113 of Example 10 was used instead of Compound A-13 of Example 5. Example 22

An organic light-emitting diode was fabricated according to the same method as Example 16 except that Compound A-117 of Example 11 was used instead of Compound A-13 of Example 5. Example 23

An organic light-emitting diode was fabricated according to the same procedure as in Example 16 except that Compound A-109 of Example 12 was used instead of Compound A-13 of Example 5. Example 24

An organic light-emitting diode was fabricated according to the same method as Example 16, except that Compound B-109 of Example 13 was used instead of Compound A-13 of Example 5. Example 25

An organic light-emitting diode was fabricated according to the same method as Example 16 except that Compound A-111 of Example 14 was used instead of Compound A-13 of Example 5. Example 26

An organic light-emitting diode was fabricated according to the same method as Example 16 except that Compound B-111 of Example 15 was used instead of Compound A-13 of Example 5. Comparative example 2

The organic light-emitting diode was fabricated according to the same method as in Example 4 except that CBP of the following structure was used instead of the compound A-13 of Example 5.

The structures of NPB, BAlq, CBP, and (piq) ₂ Ir(acac) used for the production of organic light-emitting diodes are as follows. Assessment 2 : Performance Measurement of Organic Light Emitting Diodes

The current density and luminance variation as a function of voltage and luminous efficiency of each of the organic light-emitting diodes according to Examples 16 to 26 and Comparative Example 2 were measured.

Specifically, measurements were made in the following methods, and the results are provided in Table 2 below. (1) Measurement of current density change with voltage change The measured organic light-emitting diode was measured while increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400). The value of the current flowing in the unit device, and dividing the measured current value by the area to obtain a result. (2) Measuring the change in luminance as a function of voltage. While using a luminance meter (Minolta Cs-1000A) to increase the voltage from 0 V to 10 V, the organic light-emitting diode manufactured by the brightness measurement is brightness. (3) Measurement of light emission efficiency by using the luminance from entry (1) and item (2), the current density and voltage (V) to calculate the current efficiency at ^{(10 mA / cm 2) (} cd / A) at the same current density. (4) Measurement lifetime The time required until the current efficiency (cd/A) was lowered to 90% was measured while maintaining the luminance (cd/m ² ) at 5000 cd/m ² to obtain the lifetime. (Table 2)

Referring to Table 2, the organic light-emitting diodes according to Examples 16 to 26 exhibited significantly improved driving voltage, luminous efficiency, energy efficiency, and lifetime compared to Comparative Example 2.

While the present invention has been described in connection with the exemplary embodiments of the present invention, it is understood that the invention is not limited to the disclosed embodiments, but instead, is intended to cover the scope of the appended claims. Various modifications and equivalent arrangements within the spirit and scope. Therefore, the above embodiments are to be considered as illustrative, but not limiting in any way.

100, 200‧‧‧ Organic Light Emitting Diodes
105‧‧‧Organic layer
110‧‧‧ cathode
120‧‧‧Anode
130‧‧‧Lighting layer
140‧‧‧ hole auxiliary layer

1 and 2 are cross-sectional views showing an organic light emitting diode according to various embodiments.

100‧‧‧Organic Luminescent Diodes

105‧‧‧Organic layer

110‧‧‧ cathode

120‧‧‧Anode

130‧‧‧Lighting layer

Claims (10)

An organic compound represented by the following Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, X is O, S, CR ^a R ^b or SiR ^c R ^d , Y is N or CR ^e , at least one Y is N, and Ar ¹ is a substituted or unsubstituted fused ring, R ^a to R ^{d are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C12 aryl , substituted or unsubstituted C3 to C12 heterocyclic group or a combination thereof, R ^e is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 naphthenic a substituted, unsubstituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group or a combination thereof, and a substituted group means an anthracene, a halogen, a hydroxyl group, an amino group, a C1 group To C30 amine, nitro, C1 to C40 alkyl, C1 to C30 alkyl, C1 to C10 alkylalkyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C3 a group substituted with at least one hydrogen to a C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, a carboxyl group, or a combination thereof. The organic compound of claim 1, wherein Ar ¹ is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, substituted or Unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl or substituted or unsubstituted tert-triphenyl, and substituted groups refer to hydrazine, halogen, hydroxy, amino, C1 to C30 amine, nitro, C1 to C40 alkyl, C1 to C30 alkyl, C1 to C10 alkylalkyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C3 to A group in which at least one hydrogen is substituted by a C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, a carboxyl group or a combination thereof. The organic compound according to claim 1, wherein Ar ¹ is a group selected from the group 1 below: [Group 1] Wherein, in Group 1, R ¹ to R ^{9 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or Unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted C4 to C30 arylamino group, wherein substituted group means halogen, cyanide a group substituted with a group, a hydroxyl group, an amine group, a nitro group, a carboxyl group or a combination thereof, and * represents a point of attachment to the chemical formula 1. The organic compound according to claim 1, wherein at least R ^e in Chemical Formula 1 includes a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group or Its combination. The organic compound according to claim 1, wherein the organic compound is represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] Wherein, in Chemical Formula 2 or Chemical Formula 3, X is O, S, CR ^a R ^b or SiR ^c R ^d , and Ar ¹ is a substituted or unsubstituted fused ring, R ^a to R ^d , R ^e1 and R ^e2 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or The unsubstituted C3 to C30 heterocyclic group or a combination thereof, and the substituted group means an anthracene, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, a nitro group, a C1 to C40 alkyl group, a C1 to C30 alkane. Base, C1 to C10 alkyldecyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C3 to C30 heterocyclic, C1 to C20 alkoxy, C1 to C10 trifluoro A group in which at least one hydrogen is substituted with an alkyl group, a cyano group, a carboxyl group, or a combination thereof. The organic compound according to claim 5, wherein at least one of R ^e1 and R ^e2 includes a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group. Or a combination thereof. The organic compound according to claim 5, wherein at least one of R ^e1 and R ^e2 is represented by the following chemical formula A: [Chemical Formula A] *-L-Ar ² wherein, in Chemical Formula A, * represents a chemical formula 2 or a point of attachment of the formula 3, L is a single bond, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 An alkylene group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 extended aryl group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, A combination thereof or a combination of the aforementioned groups, Ar ² includes one of the groups listed in Group 2 below: [Group 2] Wherein, in Group 2, R ¹⁰ to R ^{75 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or Unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted C4 to C30 arylamino group, wherein substituted group means halogen, cyanide a group substituted with a group, a hydroxyl group, an amine group, a nitro group, a carboxyl group or a combination thereof, * represents a point of attachment to L, and the substituted group means an anthracene, a halogen, a hydroxyl group, an amino group, a C1 to C30 amine group, Nitro, C1 to C40 alkyl, C1 to C30 alkyl, C1 to C10 alkylalkyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C3 to C30 heterocyclic a group in which at least one hydrogen is substituted by a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, a carboxyl group or a combination thereof. The organic compound according to claim 1, wherein the organic compound is represented by one of the following Chemical Formula 4 to Chemical Formula 35: [Chemical Formula 4] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 9] [Chemical Formula 11] [Chemical Formula 11] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 17] [Chemical Formula 19] [Chemical Formula 19] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25] [Chemical Formula 25] [Chemical Formula 27] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 34] [Chemical Formula 34] [Chemical Formula 35] Wherein, in Chemical Formula 4 to Chemical Formula 35, R ¹ to R ^{9 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted C4 to C30 arylamino group, wherein the substituted group means halogen a group substituted with a cyano group, ^a hydroxyl group, an amine group, a nitro group, a carboxyl group or a combination thereof, and R ^a to R ^d , R ^e1 and R ^{e2 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkane a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof, and a substituted The group refers to beryllium, halogen, hydroxyl, amino, C1 to C30 amine, nitro, C1 to C40 alkyl, C1 to C30 alkyl, C1 to C10 alkylalkyl, C3 to C30 cycloalkyl, C3 a group substituted with at least one hydrogen to a C30 heterocycloalkyl group, a C6 to C30 aryl group, a C3 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, a carboxyl group, or a combination thereof. An organic optoelectronic device comprising: an anode and a cathode opposite to each other; and at least one organic layer between the anode and the cathode, wherein the organic layer is included in items 1 to 8 of the patent application scope An organic compound as claimed in any one of the preceding claims. A display device comprising the organic optoelectric device according to claim 9 of the patent application.